IE46119B1 - Imidazoline derivatives and their use as pesticides - Google Patents

Imidazoline derivatives and their use as pesticides

Info

Publication number: IE46119B1
Authority: IE; Ireland
Prior art keywords: compound; formula; alkyl; imidazoline; dimethylphenoxymethyl
Prior art date: 1976-12-20

Application number

IE2569/77A

Other languages

English (en)

Other versions

IE46119L (en

Original Assignee

Wellcome Found

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-12-20

Filing date

1977-12-19

Publication date

1983-02-23

1976-12-20 Priority claimed from GB53059/76A external-priority patent/GB1592649A/en

1977-12-19 Application filed by Wellcome Found filed Critical Wellcome Found

1978-06-20 Publication of IE46119L publication Critical patent/IE46119L/xx

1983-02-23 Publication of IE46119B1 publication Critical patent/IE46119B1/en

Links

239000000575 pesticide Substances 0.000 title abstract description 4
150000002462 imidazolines Chemical class 0.000 title description 3
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 101
239000000203 mixture Substances 0.000 claims abstract description 38
125000000217 alkyl group Chemical group 0.000 claims abstract description 33
-1 tri-substituted phenyl Chemical group 0.000 claims abstract description 33
238000009472 formulation Methods 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 27
125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
125000003118 aryl group Chemical group 0.000 claims abstract description 20
230000000361 pesticidal effect Effects 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
125000004104 aryloxy group Chemical group 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000001424 substituent group Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
150000002431 hydrogen Chemical class 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
125000005110 aryl thio group Chemical group 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 24
239000002585 base Substances 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 10
241000607479 Yersinia pestis Species 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
150000002825 nitriles Chemical class 0.000 claims description 7
241000238421 Arthropoda Species 0.000 claims description 6
150000001409 amidines Chemical class 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 4
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
JNCWBAPRGSQFOP-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-phenyl-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC=CC=2)=C1C JNCWBAPRGSQFOP-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
239000000843 powder Substances 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Chemical group 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
150000001718 carbodiimides Chemical class 0.000 claims description 2
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
150000002540 isothiocyanates Chemical class 0.000 claims description 2
150000007530 organic bases Chemical group 0.000 claims description 2
150000002905 orthoesters Chemical class 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 8
ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
NRIWPNBCXDJQET-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1C NRIWPNBCXDJQET-UHFFFAOYSA-N 0.000 claims 1
101100440695 Dictyostelium discoideum corB gene Proteins 0.000 abstract description 2
229910052717 sulfur Inorganic materials 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 18
239000000243 solution Substances 0.000 description 15
239000000543 intermediate Substances 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 8
WAAAGQHQBWTGTM-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC(OCC=2NCCN=2)=C1C WAAAGQHQBWTGTM-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
241000238876 Acari Species 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 5
229960004132 diethyl ether Drugs 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000013078 crystal Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000007598 dipping method Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
VYKNVAHOUNIVTQ-UHFFFAOYSA-N 1,2,2,3,3-pentamethylpiperidine Chemical compound CN1CCCC(C)(C)C1(C)C VYKNVAHOUNIVTQ-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000007787 solid Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
KHSARZOABTYDBM-UHFFFAOYSA-N (2,3-dimethylphenyl) carbonochloridate Chemical compound CC1=CC=CC(OC(Cl)=O)=C1C KHSARZOABTYDBM-UHFFFAOYSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
VPLGRXGZRMQYIS-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine;hydrochloride Chemical compound Cl.CC1CCCN(C)C1(C)C VPLGRXGZRMQYIS-UHFFFAOYSA-N 0.000 description 1
DCNGTKDQHGPECL-UHFFFAOYSA-N 1-[2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1COC1=CC=CC(C)=C1C DCNGTKDQHGPECL-UHFFFAOYSA-N 0.000 description 1
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
DFPMMPAKMCFOPF-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-1-methylsulfonyl-4,5-dihydroimidazole Chemical compound CC1=CC=CC(OCC=2N(CCN=2)S(C)(=O)=O)=C1C DFPMMPAKMCFOPF-UHFFFAOYSA-N 0.000 description 1
KBLNENPYDLTIII-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n,n-dimethyl-4,5-dihydroimidazole-1-carbothioamide Chemical compound CN(C)C(=S)N1CCN=C1COC1=CC=CC(C)=C1C KBLNENPYDLTIII-UHFFFAOYSA-N 0.000 description 1
PLEIFIQIRCPPFT-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-methyl-4,5-dihydroimidazole-1-carbothioamide Chemical compound CNC(=S)N1CCN=C1COC1=CC=CC(C)=C1C PLEIFIQIRCPPFT-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000238679 Amblyomma Species 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241001649229 Psoroptes Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000002390 adhesive tape Substances 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
244000078703 ectoparasite Species 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000004519 grease Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
SQSDROHUXRMXIY-UHFFFAOYSA-N methyl 2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxylate Chemical compound COC(=O)N1CCN=C1COC1=CC=CC(C)=C1C SQSDROHUXRMXIY-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
OJEIZKGNPOLYCZ-UHFFFAOYSA-N n-(2,3-dichlorophenyl)-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1C OJEIZKGNPOLYCZ-UHFFFAOYSA-N 0.000 description 1
JTXAZQHDLZCJGE-UHFFFAOYSA-N n-cyclohexyl-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC2CCCCC2)=C1C JTXAZQHDLZCJGE-UHFFFAOYSA-N 0.000 description 1
125000005609 naphthenate group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000005359 phenoxyalkyl group Chemical group 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000003019 stabilising effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IE2569/77A 1976-12-20 1977-12-19 Imidazoline derivatives and their use as pesticides IE46119B1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB5306276		1976-12-20
GB53059/76A GB1592649A (en)	1976-12-20	1976-12-20	Imidazoline derivatives and their use as pesticides
GB4448577		1977-10-26

Publications (2)

Publication Number	Publication Date
IE46119L IE46119L (en)	1978-06-20
IE46119B1 true IE46119B1 (en)	1983-02-23

Family

ID=27259848

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE2569/77A IE46119B1 (en)	1976-12-20	1977-12-19	Imidazoline derivatives and their use as pesticides

Country Status (18)

Country	Link
JP (1)	JPS5395968A (it)
AR (1)	AR225271A1 (it)
AU (1)	AU521328B2 (it)
BR (1)	BR7708431A (it)
CA (1)	CA1108620A (it)
CH (1)	CH642821A5 (it)
DE (1)	DE2756639A1 (it)
DK (1)	DK565277A (it)
ES (2)	ES465208A1 (it)
FR (1)	FR2374308A1 (it)
IE (1)	IE46119B1 (it)
IL (1)	IL53640A (it)
IT (1)	IT1093073B (it)
LU (1)	LU78718A1 (it)
MC (1)	MC1173A1 (it)
NL (1)	NL7714063A (it)
NZ (1)	NZ186028A (it)
SE (1)	SE444563B (it)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5484575A (en) *	1977-10-26	1979-07-05	Wellcome Found	Imidazoline compound*its manufacture and insecticide composition
ZA787351B (en) *	1978-06-19	1980-08-27	Wellcome Found	Imidazolines,their preparation,intermediates therefor,and pesticidal formulations and use of the imidazolines
US4241075A (en)	1978-09-27	1980-12-23	Ciba-Geigy Corporation	Acaricidal 1-alkylthio-substituted and 1-phenylthio substituted 2-(phenoxyalkyl)-2-imidazolines
US4232011A (en) *	1978-11-02	1980-11-04	Ciba-Geigy Corporation	1-Phosphorylated 2-(phenoxyalkyl)-2-imidazoline derivatives and their use in pest control
US4379147A (en)	1981-02-09	1983-04-05	Ciba-Geigy Corporation	Substituted 2-(anilinomethyl)-2-imidazoline derivatives, compositions containing these derivatives, and the use thereof for combating pests
US4719223A (en) *	1985-10-31	1988-01-12	Smithkline Beckman Corporation	Imidazolethiol dopamine-beta-hydroxylase inhibitors
US5584888A (en) *	1994-08-31	1996-12-17	Miracle; Gregory S.	Perhydrolysis-selective bleach activators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH529766A (de) *	1967-02-23	1972-10-31	Horst Prof Baganz	Verfahren zur Herstellung von Aryloxy-isoalkyl- 2-imidazolinen

1977
- 1977-12-19 FR FR7738217A patent/FR2374308A1/fr active Granted
- 1977-12-19 NL NL7714063A patent/NL7714063A/xx not_active Application Discontinuation
- 1977-12-19 DE DE19772756639 patent/DE2756639A1/de not_active Withdrawn
- 1977-12-19 IL IL53640A patent/IL53640A/xx unknown
- 1977-12-19 CA CA293,379A patent/CA1108620A/en not_active Expired
- 1977-12-19 NZ NZ186028A patent/NZ186028A/xx unknown
- 1977-12-19 MC MC771273A patent/MC1173A1/fr unknown
- 1977-12-19 JP JP15280077A patent/JPS5395968A/ja active Pending
- 1977-12-19 IE IE2569/77A patent/IE46119B1/en unknown
- 1977-12-19 BR BR7708431A patent/BR7708431A/pt unknown
- 1977-12-19 LU LU78718A patent/LU78718A1/xx unknown
- 1977-12-19 CH CH1557577A patent/CH642821A5/de not_active IP Right Cessation
- 1977-12-19 DK DK565277A patent/DK565277A/da not_active Application Discontinuation
- 1977-12-19 AR AR270423A patent/AR225271A1/es active
- 1977-12-19 IT IT7752276A patent/IT1093073B/it active
- 1977-12-19 SE SE7714407A patent/SE444563B/sv not_active IP Right Cessation
- 1977-12-19 AU AU31747/77A patent/AU521328B2/en not_active Expired
- 1977-12-19 ES ES465208A patent/ES465208A1/es not_active Expired
1978
- 1978-09-16 ES ES473432A patent/ES473432A1/es not_active Expired

Also Published As

Publication number	Publication date
BR7708431A (pt)	1978-08-15
MC1173A1 (fr)	1978-09-25
AU3174777A (en)	1979-06-28
ES473432A1 (es)	1979-04-16
FR2374308A1 (fr)	1978-07-13
SE444563B (sv)	1986-04-21
IL53640A0 (en)	1978-03-10
JPS5395968A (en)	1978-08-22
DK565277A (da)	1978-06-21
ES465208A1 (es)	1979-01-01
DE2756639A1 (de)	1978-06-22
CH642821A5 (en)	1984-05-15
IT1093073B (it)	1985-07-19
CA1108620A (en)	1981-09-08
NZ186028A (en)	1980-08-26
IE46119L (en)	1978-06-20
FR2374308B1 (it)	1982-10-15
AR225271A1 (es)	1982-03-15
SE7714407L (sv)	1978-06-21
IL53640A (en)	1982-11-30
AU521328B2 (en)	1982-03-25
NL7714063A (nl)	1978-06-22
LU78718A1 (it)	1978-07-11

Publication	Publication Date	Title
CA1111046A (en)	1981-10-20	Imidazoline derivatives and their salts
US4226876A (en)	1980-10-07	Arthropodicidal imidazoline derivatives
US4182624A (en)	1980-01-08	Imidazole carboxylic acids and derivatives thereof
US5134145A (en)	1992-07-28	Pesticidal pyrimidinyl benzoic acids and esters
US4543413A (en)	1985-09-24	Sulphonyl derivatives of N-phenyl pyridineamines
US4414223A (en)	1983-11-08	Pesticidal anilinomethylimidazolines
IL44710A (en)	1977-12-30	1-phenyl-2-azolyl-formamidines their preparation and their use as herbicides
US3707477A (en)	1972-12-26	1,1,1-trichloro-2-amido-2-amino-ethanes
CA1108620A (en)	1981-09-08	Imidazolines
GB1592649A (en)	1981-07-08	Imidazoline derivatives and their use as pesticides
US4320125A (en)	1982-03-16	Thiazolylidene-oxo-propionitrile salts and insecticidal compositions containing these salts
GB2023603A (en)	1980-01-03	Pesticidal imidazolines, and their preparation and use
DE2614189A1 (de)	1977-10-20	Therapeutisch wirksame ureido- und semicarbazido-derivate des tiazols und verfahren zu ihrer herstellung
EP0665841B1 (en)	1996-07-17	Herbicidal pyrazolyloxy-picolinamides
SU725557A1 (ru)	1980-03-30	Способ получени 1,2,3-тиадиазол5-ил-мочевин
IL39395A (en)	1977-04-29	Oxazolidine and thiazolidine 2-(or4)-carbamoyloxime derivatives preparation thereof and compositions containing the
CA1060464A (en)	1979-08-14	Pesticidal triazapentadienes
GB1593276A (en)	1981-07-15	Imidazoline derivatives and their use as pesticides
US4874786A (en)	1989-10-17	Cyanoacetamido-derivatives having a fungicidal activity
US3637729A (en)	1972-01-25	Perfluoroalkanesulfonamides n-substituted by heterocyclic groups
DE3330603A1 (de)	1985-03-21	Neue 2-amino-alkenylsulfonylharnstoffe
JPS6335554A (ja)	1988-02-16	Ｎ−（２−シアノ−２−オキシミノアセチル）−アミノニトリル
CA1108621A (en)	1981-09-08	Pesticidal imidazolines
EP0276721A1 (de)	1988-08-03	2-Cyan-2-oximino-acetamide
US3801588A (en)	1974-04-02	Certain perfluoroalkylsulfon-amidothiazoles